Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin

FEBS Journal

Volumn 272, Issue 24, 2005, Pages 6287-6296

  Bocedi, Alessio ^a   Notari, Stefania ^a   Menegatti, Enea ^b   Fanali, Gabriella ^c   Fasano, Mauro ^c   Ascenzi, Paolo ^a,d  

^a NATIONAL INSTITUTE FOR INFECTIOUS DISEASES L SPALLANZANI   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

^c UNIVERSITY OF INSUBRIA   (Italy)

^d ROMA TRE UNIVERSITY   (Italy)

Author keywords

Allostery; Anti HIV drugs; Ferric heme; Human serum albumin; Ligand binding

Indexed keywords

ABACAVIR; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ATAZANAVIR; DIDANOSINE; EFAVIRENZ; EMTRICITABINE; HEME; HUMAN SERUM ALBUMIN; LAMIVUDINE; NELFINAVIR; NEVIRAPINE; PLASMA PROTEIN; RITONAVIR; SAQUINAVIR; STAVUDINE; ZIDOVUDINE;

ALLOSTERISM; ARTICLE; DRUG BINDING; DRUG PROTEIN BINDING; PRIORITY JOURNAL; THERMODYNAMICS;

ALLOSTERIC REGULATION; ANTI-HIV AGENTS; BINDING SITES; HEME; HUMANS; KINETICS; PROTEIN BINDING; SERUM ALBUMIN;

HUMAN IMMUNODEFICIENCY VIRUS;

EID: 29144461887     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2005.05015.x     Document Type: Article

References (57)

1. Peters T Jr, ed (1996) All About Albumin: Biochemistry, Genetics and Medical Applications. Academic Press, San Diego, CA and London, UK.
2. Sudlow G, Birkett DJ & Wade DN (1975) The characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol 11, 824-832.
3. Curry S (2002) Beyond expansion: structural studies on the transport roles of human serum albumin. Vox Sang 83 (Suppl. 1), 315-319.
4. Vallner JJ (1977) Binding of drugs by albumin and plasma protein. J Pharm Sci 66, 447-465.
5. Kragh-Hansen U (1981) Molecular aspects of ligand binding to serum albumin. Pharmacol Rev 33, 17-53.
6. Bertucci C & Domenici E (2002) Reversible and covalent binding of drugs to human serum albumin: methodological approaches and physiological relevance. Curr Med Chem 9, 1463-1481.
7. Carter DC & Ho JX (1994) Structure of serum albumin. Adv Protein Chem 45, 153-203.
8. Spector AA (1975) Fatty acid binding to plasma albumin. J Lipid Res 16, 165-179.
9. Hamilton JA (2004) Fatty acid interactions with proteins: what X-ray crystal and NMR solution structures tell us. Prog Lipid Res 43, 177-199.
10. Kragh-Hansen U, Chuang VT & Otagiri M (2002) Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biol Pharm Bull 25, 695-704.
11. Monzani E, Bonafè B, Fallarini A, Redaelli C, Casella L, Minchiotti L & Galliano M (2001) Enzymatic properties of hemalbumin. Biochim Biophys Acta 1547, 302-312.
12. Sakurai Y, Ma SF, Watanabe H, Yamaotsu N, Hirono S, Kurono Y, Kragh-Hansen U & Otagiri M (2004) Esterase-like activity of serum albumin: characterization of its structural chemistry using p-nitrophenyl esters as substrates. Pharm Res 21, 285-292.
13. Komatsu T, Ohmichi N, Zunszain PA, Curry S & Tsuchida E (2004) Dioxygenation of human serum albumin having a prosthetic heme group in a tailor-made heme pocket. J Am Chem Soc 126, 14304-14305.
14. Carter DC, Ho JX & Rüker F (1999) Oxygen-transporting albumin-based blood replacement composition and blood volume expander. US Patent No 5 948 609.
15. He X & Carter DC (1992) Atomic structure and chemistry of human serum albumin. Nature 358, 209-215.
16. Sugio S, Kashima A, Mochizuki S, Noda M & Kobayashi K (1999) Crystal structure of human serum albumin at 2.5 A resolution. Protein Eng 12, 439-446.
17. Petitpas I, Bhattacharya AA, Twine S, East M & Curry S (2001) Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I. J Biol Chem 276, 22804-22809.
18. Bhattacharya AA, Curry S & Franks NP (2000) Binding of the general anesthetics propofol and halothane to human serum albumin. High resolution crystal structures. J Biol Chem 275, 38731-38738.
19. Ghuman J, Zunszain PA, Petitpas I, Bhattacharya AA, Otagiri M & Curry S (2005) Structural basis of the drug-binding specificity of human serum albumin. J Mol Biol 353, 38-52.
20. Wardell M, Wang Z, Ho JX, Robert J, Rüker F, Ruble J & Carter DC (2002) The atomic structure of human methemalbumin at 1.9 Å. Biochem Biophys Res Commun 291, 813-819.
21. Zunszain PA, Ghuman J, Komatsu T, Tsuchida E & Curry S (2003) Crystal structural analysis of human serum albumin complexed with hemin and fatty acid. BMC Struct Biol 3, 6.
22. 13C NMR study. Proc Natl Acad Sci USA 81, 3718-3722.
23. Curry S, Mandelkov H, Brick P & Franks N (1998) Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat Struct Biol 5, 827-835.
24. Bhattacharya AA, Grüne T & Curry S (2000) Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J Mol Biol 303, 721-732.
25. Petitpas I, Petersen CE, Ha CE, Bhattacharya AA, Zunszain PA, Ghuman J, Bhagavan NV & Curry S (2003) Structural basis of albumin-thyroxine interactions and familial dysalbuminemic hyperthyroxinemia. Proc Natl Acad Sci USA 100, 6440-6445.
26. Ascenzi P, Bocedi A, Bolli A, Fasano M, Notari S & Polticelli F (2005) Allosteric modulation of monomeric proteins. Biochem Mol Biol Educ 33, 169-176.
27. Janssen LH, Van Wilgenburg MT & Wilting J (1981) Human serum albumin as an allosteric two-state protein. Evidence from effects of calcium and warfarin on proton binding behaviour. Biochim Biophys Acta 669, 244-250.
28. Wilting J, van der Giesen WF, Janssen LH, Weideman MM, Otagiri M & Perrin JH (1980) The effect of albumin conformation on the binding of warfarin to human serum albumin. The dependence of the binding of warfarin to human serum albumin on the hydrogen, calcium, and chloride ion concentrations as studied by circular dichroism, fluorescence, and equilibrium dialysis. J Biol Chem 255, 3032-3037.
29. Diana FJ, Veronich K & Kapoor AL (1989) Binding of nonsteroidal anti-inflammatory agents and their effect on binding of racemic warfarin and its enantiomers to human serum albumin. J Pharm Sci 78, 195-199.
30. Dockal M, Carter DC & Rüker F (1999) The three recombinant domains of human serum albumin. Structural characterization and ligand binding properties. J Biol Chem 274, 29303-29310.
31. Fitos I, Visy J, Simonyi M & Hermansson J (1999) Stereoselective allosteric binding interaction on human serum albumin between ibuprofen and lorazepam acetate. Chirality 11, 115-120.
32. Yamasaki K, Maruyama T, Yoshimoto K, Tsutsumi Y, Narazaki R, Fukuhara A, Kragh-Hansen U & Otagiri M (1999) Interactive binding to the two principal ligand binding sites of human serum albumin: effect of the neutral-to-base transition. Biochim Biophys Acta 1432, 313-323.
33. Dockal M, Chang M, Carter DC & Rüker F (2000) Five recombinant fragments of human serum albumin. Tools for the characterization of the warfarin binding site. Protein Sci 9, 1455-1465.
34. Baroni S, Mattu M, Vannini A, Cipollone R, Aime S, Ascenzi P & Fasano M (2001) Effect of ibuprofen and warfarin on the allosteric properties of haem-human serum albumin. A spectroscopic study. Eur J Biochem 268, 6214-6220.
35. Fasano M, Baroni S, Vannini A, Ascenzi P & Aime S (2001) Relaxometric characterization of human hemalbumin. J Biol Inorg Chem 6, 650-658.
36. Mattu M, Vannini A, Coletta M, Fasano M & Ascenzi P (2001) Effect of bezafibrate and clofibrate on the heme-iron geometry of ferrous nitrosylated heme-human serum albumin: an EPR study. J Inorg Biochem 84, 293-296.
37. Chuang VTG & Otagiri M (2002) How do fatty acids cause allosteric binding of drugs to human serum albumin? Pharm Res 19, 1458-1464.
38. Fitos I, Visy J & Kardos J (2002) Stereoselective kinetics of warfarin binding to human serum albumin: effect of an allosteric interaction. Chirality 14, 442-448.
39. Ascenzi P, Bocedi A, Notari S, Menegatti E & Fasano M (2005) Heme impairs allosterically drug binding to human serum albumin Sudlow's site I. Biochem Biophys Res Commun 334, 481-486.
40. Fanali G, Fesce R, Agrati C, Ascenzi P & Fasano M (2005) Allosteric modulation of myristate and Mn (III) heme binding to human serum albumin. Optical and NMR spectroscopy characterization. FEBS J 272, 4672-4683.
41. Bocedi A, Notari S, Narciso P, Bolli A, Fasano M & Ascenzi P (2004) Binding of anti-HIV drugs to human serum albumin. IUBMB Life 56, 609-614.
42. Sukowska A, Bojko B, Ro'wnicka J & Sukowski W (2004) Competition of drugs to serum albumin in combination therapy. Biopolymers 74, 256-262.
43. Maes V, Engelborghs Y, Hoebeke J, Maras Y & Vercruysse A (1982) Fluorimetric analysis of the binding of warfarin to human serum albumin. Equilibrium and kinetic study. Mol Pharmacol 21, 100-107.
44. Antonini E & Brunori M (1971) Hemoglobin and Myoglobin in their Reactions with Ligands, pp. 153-187. North-Holland Publishing Co, Amsterdam and London.
45. Molla A, Vasavanonda S, Kumar G, Sham HL, Johnson M, Grabowski B, Denissen JF, Kohlbrenner W, Plattner JJ, Leonard JM, et al. (1998) Human serum attenuates the activity of protease inhibitors toward wild-type and mutant human immunodeficiency virus. Virology 250, 255-262.
46. Gaudreau S, Neaut JF & Tajmir-Riahi HA (2002) Interaction of AZT with human serum albumin studied by capillary electrophoresis, FTIR and CD spectroscopic methods. J Biomol Struct Dyn 19, 1007-1014.
47. Schön A, del Mar Ingaramo M & Freire E (2003) The binding of HIV-1 protease inhibitors to human serum proteins. Biophys Chem 105, 221-230.
48. Adams PA & Berman MC (1980) Kinetics and mechanism of the interaction between human serum albumin and monomeric haemin. Biochem J 191, 95-102.
49. Kharitonov VG, Sharma VS, Magde D & Koesling D (1997) Kinetics of nitric oxide dissociation from five- and six-coordinate nitrosyl hemes and heme proteins, including soluble guanylate cyclase. Biochemistry 36, 6814-6818.
50. Wyman J (1964) Linked functions and reciprocal effects in hemoglobin: a second look. Adv. Protein Chem 19, 223-286.
51. Di Cera E (1994) Linkage thermodynamics. Methods Enzymol 232, 655-683.
52. Chen RF (1967) Removal of fatty acids from serum albumin by charcoal treatment. J Biol Chem 242, 173-181.
53. Sogami M & Foster JF (1968) Isomerization reactions of charcoal-defatted bovine plasma albumin. The N-F transition and acid expansion. Biochemistry 7, 2172-2182.
54. Cabrera-Crespo J, Goncalves VM, Martins EA, Grellet S, Lopes AP & Raw I (2000) Albumin purification from human placenta. Biotechnol Appl Biochem 31, 101-106.
55. Anderson SR & Antonini E (1968) The binding of carbon monoxide by human hemoglobin. Proof of validity of the spectrophotometric method and direct determination of the equilibrium. J Biol Chem 243, 2918-2920.
56. 2S solubility via the reaction with ferric hemoglobin I from the bivalve mollusc Lucina pectinata. Biochim Biophys Acta 1523, 206-208.
57. Guex N & Peitsch MC (1997) Swiss-model and the Swiss-PdbViewer: an environment for comparative protein modeling. Electrophoresis 18, 2714-2723.